Throughout my career journey that is broad in scope, I can say I’ve met and worked with a number of not only impressive but successful business people. We characterize someone as successful if they have risen to executive levels in a larger company or especially if they have started a business, which they in turn nurtured into something substantial. Those of us who aspire to similar greatness like to study them either from up close or by reading books to see if we can develop a profile of commonalities that make them stand out.

What comes out of such examination is typically an audit of their personality, their soft skills and the high-impact habits they have formed, with of course a cursory nod to some of the more hard/technical skills that they brought to the table to jump start it all. We celebrate their future vision, their drive and resilience, and their ability to lead and inspire teams beneath and around them.

I’m on board with all of this but won’t be headed in such a direction in this article in terms of how to profile successful people. For marketers specifically, I have already written a few articles on soft skills and personality types that tend to enable success in this profession. I have also recently posted about some of the markers of potential in a candidate with an otherwise lean resume. Nope, as usual, you can expect me to look past what has already been written as I discover and share my own brand of unique insight.

Entrepreneurs are the most fascinating study. The corporate world is more predictable, filled with type As groomed to think, dress and talk alike; to be above average although not always spectacular or differentiated. By contrast, anyone can be a self-proclaimed entrepreneur, so if you network in that territory, you’ll be exposed to quite the collage of characters and talent.

And then one thing becomes apparent – they either get it or they don’t. I think you know what I mean. For me, the tell-tale signs that they can really make it lie in how their mind works, which is the subject of this article.

Being a true entrepreneur today depends much less on tech or soft skills than it has in the past. I would never have looked at Jobs, Gates, Bezos, Brin or Zuckerberg as the best leaders with personalities that both inspire and massage my self-esteem. Few would even argue that today’s tech powerbrokers are even at the top of their class as coders or UX experts. But they have just enough of the ordinary raw ingredients to do extraordinary things. For if we characterize their mind in tech terms, they not only have decent software components but also superior APIs; their net impact is primarily generated by how their mind functions in these particular ways:

They can see the future.

Never before has this mattered as much as it does now. Technology has sped up the business life cycle in ways we could never have imagined 30 years ago. Back then, you could start a company and scale up at a measured pace, taking decades to max out your business model. And I mean ‘model’. Singular. You could marginalize your growth and take careful steps because no one else was threatening to pass you.

Now we communicate more readily (and often!). We scale up swiftly. We engage sophisticated decision support systems to adapt to changing market forces at lightning pace. The notion of a five year business plan is beyond laughable…that is, unless you can predict how we will do business and how consumers will react to products and services tomorrow, next week or next year.

Predicting the future is not only about dreaming; it’s about disciplined dreaming. I, myself, have taken a stab at envisioning The Next Generation Workplace. Regardless of the aspect of the future you forecast, you must be able to consider environmental vectors as they are today while catching new ones at the earliest signs…and then extrapolate these information bits to sensibly shape a vision of how that part of the business world will look tomorrow. It’s not easy; there are many moving pieces. How you see them interrelating will give you a leg up on designing new products or adapting your company culture. Because for a company to consistently grow, this is a never-ending process.

They create viable business models with the mind of a web crawler.

I’m thinking mostly of the startup space here although the concept definitely applies if you are considering launching a companion business to your existing one.

All of us would agree that there are many things to consider, many questions to ask, many decisions to make when cooking up a business idea. So, we work through the process, sorting through all the elements. Old school models still apply, so we hash out our Cs and our Ps and navigate the Porter model of power within the value chain. We know we must be good/different/better. We check in with people whose opinions we trust and we adapt based on advice and learning.

The more arduous and clunky this journey feels to you, the less developed is your business mind compared to a natural entrepreneur.  Only those special people can take some simple information – say, a product description and a specified target market – and instantly explode their thoughts through a complex network of business subjects. In minutes or even seconds, they can identify opportunities, challenges and critical information gaps to project if the idea is worthwhile. What’s more, they know what opportunities are big, which barriers are insurmountable and what decisions can cause a tipping point in consumer behavior or financial viability. All of these thought processes are instant and intuitive but are handled with great structure and discipline on the inside.crawler

I mean, take note of the VC process. In Canada, we have a television show called the Dragon’s Den which creates a more entertaining version of what real founders experience when scaring up some funding. You get up there, talk about your product for a few minutes, get interrupted with a few questions and it’s almost like POOF you either have an investor or you don’t. Mark Cuban has his fingerprints on a number of high and low profile startups. I can’t imagine he makes investment decisions on little more than a 2 page prospectus. What takes you six months to prepare for is vetted in 20 minutes. Why? Because these guys are like google search: you pose a question and it serves up a well-reasoned answer by crawling all of its hidden resources of knowledge, experience, intuition and plain ol’ know-how…in a nano-second.

Among the builders I’ve met, I have noted that the least sophisticated business minds fail to prioritize the consumer. Let’s put aside for a moment the potential to create new needs in the market with a breakthrough product idea; unless you are sitting on an invention on a scale of drones and virtual reality, we won’t have to go there. It mostly starts with the consumer – knowing their needs, how passionate they are about their needs, how they would like their needs served, how the competish currently serves those needs. The brilliant mind goes there immediately for the sake of designing a feasible solution and pricing it according to the passion to fill that need.

Instead, I have encountered too many founders who start with objectives that have little to do with the consumer…and are, in fact, more self-serving. Those objectives are typically financial (“I want to make a boatload of money”…and the ever-popular “I’m looking for that billion dollar idea”) or awareness related (“I have this app, now how do I get people to download it?”…and…”how can I get more traffic to my blog?”). What they get from me is a pointed speech about how commercial success – however you define it – is the byproduct of serving your consumer. And then we go from there. Point is, never mind processing all the rest of it, if you aren’t wired to even begin in the right place your journey will likely be disappointing.

You can offset your limitations by being self-aware. Know what you don’t know – what information gaps you need closed with advice or what expertise you need to acquire over the longer term. I have actually met founders with some incredible personal assets but who will likely fail at achieving their goals; they refuse to dilute their shares by onboarding a needed and credentialed catalyst for their business. Sad.

They understand people as well as concrete things.

Behind every transaction is a person. And people present a complex brand of logic, reason, feelings and emotions. Data can detect patterns and calculate probability, but it will seldom tell you why your customers do what they do, and in fact, it can often mislead you. That’s for you to figure out. I mean, there are thousands of stock market analysts out there who will never have a perfect forecasting model because of the number of transactions driven by emotion.

The exceptional entrepreneur seamlessly draws from the right and left parts of the brain; it knows how to construct and interpret research, observe behaviors, create one-to-one engagement and incorporate instinct to give the necessary context that drives high-impact product and commercialization decisions.

Mark Zuckerberg even knows enough about his consumers to delay implementation of business-building ideas. The risk with social media platforms is that once you have a critical mass of users, you as the founder become pressured to monetize your user base. Consequently,  any tactic you use (say, ads) will begin to contaminate the purity of experience that attracted engagement in the first place. The risk is disengagement or migration to another platform. In layman’s terms, you start scaring people away with your desperation to collect their money.

To mitigate this risk, Zuckerberg has refused to begin toying materially with Instagram and WhatsApp platforms until they are used more widely and engrained into everyday lives, which limits the potential to bail. Seems like a small thing but it’s a game-changing insight that will help keep the Facebook family of companies relevant for years to come.

Sometimes, businesses catch on in spite of an apparent lack of deep consumer understanding. The challenge, then, becomes sustainability if luck has been a success driver to date. I think of Tinder as a perfect example. The innovative and simple UX has been a huge factor in its adoption. Where I think they are in danger is how they have defined the business they are in.

Tinder thinks it’s a hookup app because this is the proposition they have sold to the consumers and, well, they grew, so …that must be why people use it. (OK they don’t say ‘hookup’; they use the standard industry terms like ‘meet’…and ‘locals’ etc..but still…). Here’s the interesting piece. Millennials are statistically much less promiscuous in their sexual and dating behavior than prior generations; this is counter-intuitive given how much technology has made ‘meeting’ so much simpler and sitting in a bar all night. It’s also a head scratcher given the explosion of dating apps.

The consumer / societal insight I believe Tinder is overlooking is that the greater need for millennials is approval and positive feedback. Their self-esteem rides with likes and matches. The ego needs to be fed, not so much the sexual appetite. Tinder delivers fantastic ROI by generating a high volume of approvals / matches on demand, and with negligible investment in time or cash. That’s their business model that their stats and research will never tell them directly (no focus group participant will admit to just wanting to be ‘liked’; they’ll throw up a dating objective smoke screen because it sounds better). This is why people complain that they have 20 matches yet so few talk or meet. This is why Tinder may shoot itself in the foot by throttling the number of matches you’re allowed in a day if you don’t buy Tinder Plus for $10 a month. Dear Tinder: millennials are resourceful; they’ll quickly find another avenue to service their interests. Location-based apps are popping up everywhere.

They execute seamlessly by understanding dependencies.

Once you overcome that first tough hurdle of conceiving a viable business, you will face an even bigger one, which is to upload it into the marketplace. To do this you build an infrastructure of systems, processes, finances, manpower and expertise. You also create strategies and action plans to bring it all to life. There are innumerable decisions to make along the way and all are for the sake of aligning with the vision, inciting efficient growth and fostering an inspiring workforce.

The exceptional entrepreneurial mind recognizes that almost no decision is made in a vacuum. Each decision or action taken will likely create a ripple effect. Those who don’t understand this will experience unanticipated pain from the dependencies to the point that some reverberations can take down your company. A strong entrepreneur can not only ideate but execute based on how they link the pieces together, and anticipate.

We see examples of this in every day life. I seem to find myself in a number of political and economic discussions these days, given the times. The first thing I tell people is to keep in mind that when you fix one thing, you break something else in most cases. The French thought it’d be a great idea to raise corporate taxes to maintain the revenues to fund their lifestyle. What they forgot was that they had this French-speaking EU neighbor named Switzerland which as a result had comparatively low taxes. Check the number of corporate relocations. Bye bye, jobs. I spoke earlier about tipping points; if you push hard enough and options are accessible…then…

And then all these discussions about raising the minimum wage. I’m not here to take a stand, just acknowledge consequences. We nod our head out of humanitarian support for higher pay, and that’s as far as we think. Yet, we haven’t considered how many small businesses can handle that expense without cutting staff or shutting down. We don’t think about the employees who have worked hard for their raises for the last 3 years only to have their wage gap versus new employees closed to nearly zero. None of this goes through our minds but they become all new issues to solve…and sometimes worse ones.

Can we talk about how many software implementations I’ve been through where leaders and software vendors produced the most excellent gant charts to implement software that will make work somehow more efficient? Each time, they in whole or in part overlook the fact that processes and job descriptions were now changing at the most fundamental level. What feels like implementation is actually broader organizational change; if you don’t see it in that way, you’ll slow your company’s progress while you become distracted adjusting.

Being single-minded in your decision making process while running a company is a risky situation. You can’t wait for fallout – you have to anticipate most of it. Yourself. As taxing as it sounds, you must have a natural orientation to question the impact of all key decisions on time, people, money and all aspects of your business universe. The entrepreneur’s mind stretches deep into each domain and anticipates where to focus to minimize disruption and keep the company on course.


The mind of the entrepreneur is indeed glorious. It knows where to initiate the thinking process, it stretches far and deep, it operates quickly while joyously embracing both fact and nuance. What’s more impressive is that the conclusions it draws have context, value and meaning so that it can provide guidance in changing direction, pushing through, or just plan bailing. These processes all happen seemingly at once.

Does your mind work this way or do you work through each business detail one step at a time? Do you pore through the mountainous number of tips and suggestions from those growth hacking blogs, lead generation articles and CEO interviews and try to decide which to incorporate first? Or do you have the innate tools that allow you to instantly apply logic and filters to determine what advice is right for your business to avoid the onerous process of testing and learning (industry speech for guessing)?

You may have a cool idea. You may know how to code. You may be effective with AdWords. You may be a charismatic personality. But if you want to create a viable and sustainable business, you need the beautiful mind of a genuine entrepreneur. You can condition yours at least part way through experience, observation and practice. You can seek advice and counsel. You can read books and articles. But you’ll only get so far in imitating the very natural ability to master business complexity by how you access, process, synthesize and filter all the inputs.

My advice to you relative to these skills is know what you have, develop what you can and partner to acquire the rest. That’s the best formula for success I can offer to you. Otherwise, should you choose to focus elsewhere or adopt a different philosophy, I’ll simply wish for good fortune to be your eternal companion as you take on your next big business challenge.



Check out this companion piece published in 2016 on the key to great advice.

August 2017. Epic article from a Forbes contributor on the 10 Characteristics of a Future-Facing Company. Recurring themes!